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Most Embarrassing Gaffe

Obama: Overstating a Death Toll by 9,988
On May 8, 2007, during a speech in front of 500 people in Richmond, Virginia, Obama described the damage a tornado had recently caused in Greensburg, Kansas. “In case you missed it, this week, there was a tragedy in Kansas,” he said, turning toward his supporters on the stage. “Ten thousand people died, an entire town destroyed.” Those in attendance had missed that, actually—it was twelve people who died in the tornado. Obama realized his mistake a few minutes later, explaining, “There are going to be times when I get tired. There are going to be times when I get weary. There are going to be times when I make mistakes." His blunder, while innocent, played into the notion that Obama was too inexperienced to be running for president. "The campaign will be decided on how many mistakes he makes,”' an unnamed Democratic senator told the New York Times. "The winds blow fierce when you run for president.” Unfortunate metaphor, but yes, we suppose they do.

McCain: Calling Chelsea a Dog. Yeah, He Went There
Throughout his career, McCain’s quick wit has been a double-edged sword, but it wasn’t until he disparaged the First Daughter that he really started to feel the effects of being a self-proclaimedwiseass . Speaking at a Republican event in 1998, he asked: "Why is Chelsea Clinton so ugly? Because her father is Janet Reno." The quip went over well in the room but bombed with the public the next day. McCain tried to weasel out of the controversy, saying he heard the joke on Leno, but the comedian would have none of it: "I've never, ever done a Chelsea joke nor would I. Political humor is like the Mafia—everything's open game as long as you don't go after the families." Multiple publications even refused to reprint the crack. (Maureen Dowd referred to it as the “a now-infamously ignoble joke”; the Washington Post just wrote that it was "too vicious to print.") The AP has called McCain’s mouth a WMD “that won’t quit.” It may not be a coincidence that he has changed his campaign tag from “The Straight Talk Express” to “No Surrender.”